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Chemoselective Transesterification of Methyl (Meth)acrylates Catalyzed by Sodium(I) or Magnesium(II) Aryloxides

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Title: Chemoselective Transesterification of Methyl (Meth)acrylates Catalyzed by Sodium(I) or Magnesium(II) Aryloxides
Authors: Ng, Jie Qi Browse this author
Arima, Hiro Browse this author
Mochizuki, Takuya Browse this author
Toh, Kohei Browse this author
Matsui, Kai Browse this author
Ratanasak, Manussada Browse this author
Hasegawa, Jun-Ya Browse this author →KAKEN DB
Hatano, Manabu Browse this author
Ishihara, Kazuaki Browse this author
Keywords: acrylate
DFT calculations
Issue Date: 1-Jan-2021
Publisher: American Chemical Society
Journal Title: ACS catalysis
Volume: 11
Issue: 1
Start Page: 199
End Page: 207
Publisher DOI: 10.1021/acscatal.0c04217
Abstract: A highly chemoselective transesterification of methyl (meth)acrylates catalyzed by sterically demanding 2,6-di-tert-butyl-4-methylphenol-derived NaOAr or Mg(OAr)(2) was developed. The desired transesterification proceeded without the undesired Michael additions under mild reaction conditions at 25 degrees C, and various primary and secondary alcohols, diols, triol, and tetraol on a scale of up to 10 mmol could provide the corresponding functionalized acrylates in high yields. Transition states were proposed based on monomeric and dimeric active species, and computational density functional theory calculations strongly supported high chemoselectivity to minimize undesired Michael additions.
Rights: This document is the Accepted Manuscript version of a Published Work that appeared in final form in ACS catalysis, copyright c American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see .
Type: article (author version)
Appears in Collections:触媒科学研究所 (Institute for Catalysis) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 長谷川 淳也

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